The Reward of Taking a Chance

On March 1, 1968, my law partner, Jim, and I formed a company to invest in real estate. I went out and agreed to buy houses and apartment buildings, promising down payments of $5,000 or $25,000 in thirty to sixty days. There was just one small problem. Neither Jim nor I had any money. Somehow we always came up with the down payment, but those were scary times.

After two or three years of watching me repeatedly put our financial lives at the precipice, Jim cornered me in my office one afternoon and told me that he didn’t like what I was doing.

“Jim,” I said. “Between us we have a net worth of $15,000. Suppose we take the risk, as we have, run our net worth up to $1,000,000 over the next few years then lose it all? We would have gone from almost nothing to really nothing. No big loss. But suppose we run our net worth up to a million dollars and keep it? We could be set for the rest of our lives.”

Though Jim was polite, his fear pushed him toward caution and in 1971 Jim left our company to practice law with different—and I assume more financially conservative—partners. I continued to take those same scary financial risks. It was a “bet” I eventually won.  Big time.

With women, however, I was more like Jim with money. As a high school student I could only gather enough courage to ask a girl to dance with me just as she was waltzing out the door on the arm of someone else. I was paralyzed by my fear of rejection, so I didn’t get to practice my fox trot with very many girls.

But I’ve noticed, as perhaps you have, that where you take the greatest risks you reap the greatest reward. In fact, isn’t risk the only way to achieve great reward? And risk, even great risk, is often an illusion. Here’s why.

At high school dances I doomed myself to failure for just one reason—I refused to try. No ask (no risk), no dance. No dance, no date. No date, no . . . anything. Suppose I had been more assertive? Would I have suffered total rejection? Not likely. Would I have enjoyed the pleasure of spinning around the dance floor with a girl in my arms? Yes. So if I had “taken a chance” I would have gained more at the time, and I also would have gained experience to help me later. As the poet John Dryden said, “None but the brave deserves the fair”

On a deep level we all fear rejection. I know I do. But my fear of loss is not the same as loss itself. A few years ago, at age sixty, my younger brother died of a sudden heart attack. I had always assumed that both of us would survive well into old age. I had no fear of losing David, but I lost him anyway. I’ll say it again—the fear of loss is not the same as loss itself. It is not loss itself that deters us, it is the fear of loss. And as Franklin Delano Roosevelt reminded us, “The only thing we have to fear is fear itself.”

So I encourage you to take a chance. Not blindly, but deliberately and more often than you do now. It is better to take ten risks and enjoy seven victories than to take one risk and win only once.

Take a close look at those areas in your life in which you would like “more.” More money, more friends, more travel, more anything. You might politely ask for a slightly higher increase in salary, where the real risk is a lot lower than the perceived risk. Then go for it!  (My employees do this all the time.)

You may find that there are some areas—for me, my physical safety—in which the loss could be catastrophic and you do not want to take any risk at all. That’s perfectly fine. We will never meet at the top of Mount Everest. But we might share a real estate investment. Or a dance.

Alan